Hi NidaI am very spectacle that the purchase prices you mention are anywhere but war zones.Most worth considering will start at $100K with rehab necessary.Please bewareBest Mike

Section 8 can be a solid strategy, especially in cities like Detroit where the rent-to-price ratios often make it worth considering.

Anyways, I'm seeing a lot of general speculation on here but people don't invest in these markets because they believe they're the greatest places to live in the world, they're interested in the cash flow and possible appreciation.None of my clients were talking about appreciation in the Cleveland market in 2019 and now their properties are worth 30-40% more, and that's on top of record high rent prices in this market. 

In my experience, the average Section 8 resident behaves differently than the average market rate resident, and the government-backed rent is not worth the added hassle.  

Some lenders allow exceptions for transfers to LLCs owned by the borrower, but it’s worth confirming first.Explore transfer tax exemptions: Chicago doesn’t make this easy, but there may be exemptions or reductions for certain types of ownership transfers.

Here’s a thought:Step back and evaluate which properties, if any, are truly worth keeping based on current performance and future potential.

And if they did, what's an hourly rate worth depending on their experience? 

That risk, in retrospect, is not worth the potential return.   

It's not only the money you'll lose, it's the time you spend (I figure worth $100 hr) and the mental anguish and stress.

You'll have to make some sacrifices, put in some work but I promise that its all worth it in the end.